Synthesis of acyclic nucleosides and other C-1 substituted alditols from carbohydrates using a tandem alkoxyl radical β-fragmentation–nucleophilic addition |
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| Authors: | Alicia Boto, Rosendo Hern ndez,Ernesto Su rez |
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| Affiliation: | aInstituto de Productos Naturales y Agrobiologı́a del C.S.I.C., Carretera de la Esperanza, 3., 38206 La Laguna, Tenerife, Spain |
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| Abstract: | The oxidative β-fragmentation of alkoxyl radicals generated from easily available carbohydrates is an efficient methodology to obtain acyclic nucleosides and other C-1 substituted alditols. In the reaction conditions an oxycarbenium ion is generated, which can be trapped by a variety of oxygen, carbon and nitrogen nucleophiles, in good yields and stereoselectivities. |
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| Keywords: | alcoxyl radical fragmentation diastereoselective synthesis alditols nucleosides |
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